From never-taken European trips to unspoken "I love yous," the generation that had it all reveals the surprising regrets that keep them up at night—and why your future self is desperately hoping you'll pay attention.
Remember that feeling when you're cleaning out your closet and find something you bought years ago with the tags still on? That moment of "Why didn't I just wear this when I had the chance?"
Life regrets work the same way, except we can't donate them to Goodwill.
I've spent countless hours talking with people in their 60s, 70s, and beyond. After nearly two decades analyzing financial patterns and human behavior, I shifted to writing about what really matters. And you know what I've discovered? The generation that built so much of what we have today carries some surprisingly consistent regrets.
These aren't just wistful "what-ifs." These are the hard-earned lessons from people who've lived through decades we're still navigating. So if you're wondering what you might wish you'd done differently in 20 or 30 years, here's what the boomers are telling us.
1. Prioritizing money over experiences
"I wish I'd taken that trip to Europe when I was 35 instead of putting it off until retirement," one 72-year-old told me recently. By the time she retired, her knees couldn't handle the cobblestone streets she'd dreamed of walking.
Having worked in finance for years, I get the appeal of watching numbers grow in accounts. But here's what those spreadsheets don't show: the memories you didn't make because you were waiting for the "perfect" financial moment.
The boomers I talk to don't regret the vacation they took. They regret the ones they didn't. They don't wish they'd saved an extra thousand dollars. They wish they'd used it to visit their college roommate in Australia or take their kids camping more often.
2. Not telling people how they really felt
How many times have you swallowed your words to keep the peace?
One man shared how he never told his brother how much his support meant during his divorce. His brother died suddenly at 58, and those unspoken words became permanent regrets.
Whether it's love, gratitude, or even constructive criticism that could have helped someone grow, boomers consistently wish they'd been more emotionally honest. They spent decades thinking there would always be more time for those conversations. Spoiler alert: there isn't always more time.
3. Staying in the wrong career too long
This one hits close to home. My burnout at 38 was brutal, but it forced me to reconsider everything. Many boomers weren't so lucky. They stayed in soul-crushing jobs for 30, even 40 years, always thinking they'd pursue their real passion "someday."
One woman told me she spent 35 years in accounting when she really wanted to be a teacher. By the time she retired, she felt too old and tired to start over. "I traded my dreams for a steady paycheck," she said. "The paycheck is gone now, and so is the dream."
The security they thought they were building? It came at the cost of fulfillment they can never get back.
4. Not taking care of their health sooner
"I thought I was invincible in my 40s," a 69-year-old marathon runner told me. He only started running after his first heart surgery at 61.
The story repeats itself: ignored warning signs, skipped check-ups, "I'll start exercising next month" that turned into next decade. When my own father had his heart attack at 68, he said his biggest regret was not taking his blood pressure seriously in his 50s.
Boomers consistently say they wish they'd treated their bodies like the long-term investments they actually are, not rental cars they could abuse and return.
5. Letting friendships fade
Remember your college friends who were going to be in your life forever? The work buddies who made those long days bearable?
Boomers talk about lost friendships with a particular kind of sadness. They let careers, kids, and geographic moves slowly erode connections they thought would always be there. Now, many find themselves in their 70s trying to make new friends, which is about as easy as learning TikTok dances.
One retiree put it perfectly: "I have a beautiful house and a healthy retirement account, but no one to call on a random Tuesday to grab coffee."
6. Not learning from their parents while they could
"I never asked my mom about her childhood in Poland," one woman shared, tears in her eyes. "Now she's gone, and so are all those stories."
Whether it's family recipes, origin stories, or life lessons, boomers deeply regret not mining their parents' wisdom while they had the chance. They were too busy being embarrassed by their parents' quirks to realize those quirks were actually treasures.
7. Being afraid of looking stupid
The number of boomers who tell me they wish they'd taken that dance class, learned that language, or started that business but didn't because they were afraid of looking foolish? It's heartbreaking.
One man wanted to learn guitar at 35 but thought he was too old. At 70, he realized he could have been playing for 35 years by now. The fear of temporary embarrassment cost him decades of joy.
8. Not setting boundaries with toxic people
Family members who drained them. Friends who only called when they needed something. Bosses who demanded everything and gave nothing back.
Boomers spent years, sometimes decades, letting toxic people run roughshod over their lives because they thought setting boundaries was selfish or mean. Now they realize those energy vampires stole time and peace they'll never get back.
"I spent 20 years dreading Sunday dinners with my critical mother-in-law," one woman confessed. "Twenty years! That's over a thousand Sundays I could have spent doing literally anything else."
9. Trying to be someone they weren't
The pressure to fit a certain mold was intense for boomers. Men who wanted to be stay-at-home dads. Women who didn't want children. People who realized they were LGBTQ+ but stayed closeted for decades.
The stories of lives half-lived to meet others' expectations are gut-wrenching. I learned this lesson early when I had to confront my parents' disappointment about leaving finance. But many boomers never got that chance to break free.
10. Not being present in the moment
"I was always focused on the next milestone," a retired executive told me. "First it was the next promotion, then the kids' college funds, then retirement. I never just... was."
They missed their kids' childhood while working late. They missed sunsets while checking emails. They missed conversations while planning tomorrow's to-do list.
The cruel irony? All that future they were preparing for is now their past, and they can't remember enjoying much of it.
Final thoughts
Reading through these regrets might feel heavy, but here's the gift: you're reading them now, not looking back on them later.
Every single one of these regrets is actually a roadmap for what to do differently today. That conversation you've been avoiding? That trip you keep postponing? That toxic relationship you keep tolerating?
The boomers have given us something invaluable: the chance to learn from their hindsight while we still have foresight. We don't have to wait until we're 70 to realize what really matters.
So maybe the question isn't what will you regret in 30 years. Maybe it's what will you do differently starting right now?
Because unlike that jacket with tags still on it in your closet, you can't donate your regrets. But you can decide not to collect them in the first place.
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